This is the 4th chapter in my story of the cabin boy and the pirates.
All comments are appreciated at chartoe@aol.com
Life With The Pirates - 4
The next morning the Captain and I were awaken by a loud banging on the cabin door. The Captain yelled at the man to come in and as he did he told the Captain that land had been sighted off the front of the ship. The Captain hurriedly climbed out of the cot and started getting some clean clothes on. He ordered me to get up and go to the galley and help the cook prepare a quick meal for the men. He also told me to be sure and use the bucket and clean myself up as good as I could.
As I headed to the galley I noticed that the men were busier than usual as they were making sure things were tied down and put away. There was nothing lying around that might seem out of place. I helped the cook as he prepared some fresh fruit and put on some more coffee. He also pulled out a crate that contained several bottles of wine. He had me place them on the end of the table.
I looked at him and asked what all the fuss was about. He explained that the Captain always wanted the ship to look its best when he entered a port. He said that the Captain would bring a few men aboard who might want him to carry some things for them to another island or country. He always entertained the men in the galley with wine and fruit. He also said that it appeared that I would be going ashore with the Captain and Old Joe. He told me that for my own safety to stay close to Old Joe and do exactly what he said.
Most of the men came in and grabbed a piece of bread and some meat and quickly ate it. Some of them grabbed a piece of fruit and headed outside again. The men were all busy as they helped guide the ship in next to the dock and tie it off. All most all of the men left the ship at the same time. Old Joe and the Captain came to the galley and tossed me some clothes to put on. They were large and baggy but they seemed to please the Captain and Old Joe.
We left the ship and headed toward some type of tavern from the sound of the yelling that was coming from it. I could smell the stale beer and wine that was being served in the building. As we got to the door the Captain told Old Joe to go inside as we waited for him. When he came out he pointed to our left and we started off in the direction of a small building. When we got there Old Joe used a key and unlocked the chain that was fastened to the door.
As we entered the room I noticed a bed on one side of the room with a table and chair in the middle to the room. The Captain looked inside and then whispered something to Old Joe and left the room. Old Joe looked around the room and then lit a couple of lanterns and sat down at the table. He motioned for me to take a seat and to listen to him. He told me that I was to stay in the room and when the different men visited I was to do whatever they wanted. He let me know that he would always be right out side and all I had to do was yell out his name and he would come inside and help me out.
He looked at me and wanted to know if I understood exactly what he was talking about. I told him that I understood as I started removing my clothes. He told me that there was no need to be worried that they knew most of the men around the area and knew which ones not to trust. He told me to take some of he oil he had brought with him and spread some on my asshole since that would be what most of the men wanted from me. I spread some on my hands but was not able to apply it like it should be.
Old Joe told me to bend over and spread my legs as he poured some of the oil right on my asshole. He then took his finger and pushed it inside and continued until my asshole was very slippery. He pulled his finger out and said that I was ready for anyone. He left the room as he handed me a few pieces of fruit and told me to help my self if I felt hungry.
A few minutes after Old Joe left the room I heard him outside talking with a couple of men. The door opened and a man walked in loosening his pants as he entered. I looked at him and waited for him to tell me what he wanted. I could tell by the way he stumbled across the room that he had been drinking. He looked at me and dropped his pants and told me to suck him until his cock got hard.
I dropped to my knees and placed his average size cock into my mouth and started sucking on his cock as I rolled my tongue around his cock head. His cock only took a few seconds before it was standing on its own. The man pulled his cock out of my mouth and told me to turn around and bend over. He grabbed my hips and pulled me toward him as his cock slipped up my crack and onto my back. He cussed at the situation as he pulled away from my ass and tried to push his cock into me again, and again it slid up the crack of my ass and onto my back.
I reached behind me and grabbed his cock and held it in place as he pushed again. This time his cock slipped inside my asshole as I removed my hand and braced myself on the edge of the table. He started thrusting slowly at first but as the feelings were making connection with his blurred brain he got faster. He only lasted about two minutes and he had only got me wanting more. When he pulled his cock out he slapped my ass and told me he was sorry if he had hurt me. I had to bite my lip to keep from laughing.
As he left the room another man entered. This man's cock was all ready hard when he dropped his pants so I turned my ass to him. He wasted no time as he grabbed my waist and stabbed his cock into me. The quickness of his action had caught me off guard and I let out a little yell as some pain hit me. He asked me if I was all right as he slowed down. I nodded my head to let him know I was fine as he picked his pace back up. He started driving into me with all his might as he started saying things to me in some foreign language. He lasted longer than the first man but was soon shooting his cum deep in my ass.
It was about ten minutes before the next man entered the room and as he did I noticed he had one wooden leg. He sat down on the bed and removed his pants and his wooden leg. I was more curious about his leg than I was about his cock. He noticed me looking and grabbed his cock and shook it at me and said that was what he had paid for me to pay attention to. His cock had started growing before I even sucked it into my mouth. Even though he was not what I would call a very large man in the cock area, his cock was plenty big enough for my mouth. I was just getting use to the size of his cock in my mouth when he pulled it out.
He lay back on the cot and had me straddle his cock. I slowly started feeding his cock into my asshole when he grabbed my hips and pulled me completely down on his cock. He was thrusting up into my asshole and I could feel that wanting desire start to grow in my asshole. I told him to be still and I would do all the work. He took his arms and crossed them underneath his head as he laid back and watched. I placed my hands on his chest and started pumping my ass up and down on his cock. I could tell by the grin on his face and the way he kept closing his eyes that he was enjoying my handy work. I was really getting horny as my prostate was rubbing against his cock. My cock was hard and dripping pre cum on the man's stomach.
He quickly reached up and grabbed my hips and slammed his cock as deep as he could in me. I felt his cum as it spurted out of his cock and deep in my asshole. He shot a few more times as I felt his cock start to go soft. I pulled myself off of him and moved to the door as the man replaced his wooden leg and clothes. I stuck my head out the door and called to Old Joe.
When he came to the door I told him that I really wanted dick up my ass and one man may not be enough. He looked at me and asked if I was feeling like I had last night. When I told him I was he said he would see if he could keep me satisfied. He then turned back to the group of men who had gathered outside the little building. I went back inside as the wooden legged man passed me on his way out.
I moved over to the bed wanting to jerk my cock off, but knew it would be better to wait. Old Joe came into the room with two other men and told me to hand him the pillow off of the cot. I tossed it to him as he moved the table against the wall. He then told me to lie across the table and on top of the pillow. When I did one of the men immediately pushed his cock in my ass and started fucking away.
Old Joe leaned down next to my head and said that since I was so horny that we might as well put it to good use. He said that he would be sending a man in as often as one left the room. That way I would be sure to have a cock up my ass for as long as the men held out. He then whispered that if I was still horny after the men ran out that he would come in and help me finish up.
The man in my ass was doing a pretty good job as he was rubbing my prostate and my cock was very near cumming. When he started cumming so did I. As soon as he had pulled his cock out the other man had pushed his in. When it was all the way in he started pounding so hard that the table was banging up against the wall. I heard the door as it opened and closed and felt the hands of a very big man as he started rubbing my back.
I stopped wondering about the next man when my cock was throbbing and on the verge of cumming again. The man in my ass didn't last long enough for me as he came and pulled his cock out. I felt the next man's fingers as he pushed his fingers up my dripping asshole. He then pushed his fingers inside my mouth and told me to suck them clean. I could taste the cum that he had gathered out of my asshole as I continued to suck on his fingers. He rotated his fingers a couple of times before he started feeding his cock inch by inch into my asshole.
I wanted all of him inside me then, but he really enjoyed toying with my mouth and asshole. I finally couldn't take it anymore as I thrust my ass back onto his cock. He moaned and then started slamming himself into my ass. I could tell by the way that his thighs completely covered my ass that the man fucking me now was not a little man at all. He started a rhythm where he would drive his cock against my prostate real hard about three times and then grab my hips and only thrust his hips in short quick movements.
The first time he did it I was about to cum when he started the short strokes. The next time he did it I started cumming and his short strokes were making my cock jump with each stroke. He seemed to know when my cock had stopped shooting, as he would start the hard strokes again. He did this three times before I felt his cock erupt inside my asshole. I relaxed as he pulled his cock out and was catching my breath when I felt the next cock enter my asshole. As soon as it entered my ass I wanted to push back against it. I guess the man knew what I wanted as he started pumping faster and faster. He didn't last very long and Old Joe was true to his word.
He kept a steady stream of men coming into the room and I was able to cum with almost every one of them. The only ones I didn't cum with was the ones who were either too little to rub my prostate or came to fast to get me worked up. Several times I thought I couldn't take anymore when my cock would tell me otherwise. The very next man would fit my asshole just right and my cock would be blasting again.
The last man who used my asshole was just long enough to reach my prostate but not long enough to give it the rubbing it needed to get me off. When he came I was really worked up and was about to jerk myself off when Old Joe came into the room and enquired how I was feeling. I told him that my legs were a little sore from being rammed into the table but my cock was still raring to go as I showed him. He told me that there were no more men waiting outside and if I wanted he would be glad to help me get off.
I didn't say a word as I leaned back across the table and spread my legs. He stepped back to the door and locked it. He turned around and dropped his pants and started applying some oil on his enormous cock. I started to tell him he wouldn't need the oil, but after watching his cock grow I felt it was better to be safe than sorry. He moved in behind my ass and placed the head of his cock at my now gapped open hole. When he pushed the head slid in with no pain just a little pressure.
As he continued to apply pressure his cock continued to slide inside my asshole. When about half of it was inside me I could feel the new pressure that the rest of his cock caused in my asshole. When he started pumping in and out he was rubbing my prostate in both directions. I started moaning and groaning, as the pleasure was almost too much to stand. Old Joe must have been pleased with his work in my ass, as ever so often he would slow down just to hear me yell for him to keep going.
When I started cumming the orgasm was so strong that for a few seconds everything was completely black even though I could still hear Old Joe grunting as he continued to ram his cock into me. When my vision started coming back my cock was throbbing as it had released all the cum it could at the time.
Old Joe pulled his cock out of my ass and pulled me off of the table and sat me down in the chair. He then placed the head of his cock at my mouth as he slowly worked the head inside. He didn't try to force anymore in as he grabbed the shaft of his cock and started stroking very fast. It was obvious to me that he was wanting to feed me his cum and at the time I was a willing recipient. When he started cumming I tried to swallow all of his cum but it was too much too fast. About half of it started running down the corners of my mouth and dripping off of my chin.
When he stopped cumming I pulled his cock out of my mouth and with my hand scooped up the cum around my mouth and licked it off of my fingers. Old Joe pulled on his cock again and a few drops appeared on the piss hole. I leaned over and kissed them off and gave his cock head a couple of licks.
He started dressing and asked me how I felt. I stood up and tried to walk and found that I was weaker than I felt. The more I moved around the more the strength returned to my legs. Old Joe watched me, as I seemed to get back to normal. He called me back to the table and had me lean back over as he took a cloth and washed the cum off of my legs and ass. The cool water felt great on my asshole and Old Joe commented on how red and a little swollen it appeared to him. He said that other than that it was a very cut little pussy hole. He applied some more of the oil to my asshole and said it would make it feel better.
He handed me a bottle of wine and told me to drink up but to not get drunk on it. I drank a couple of good swallows as he handed me the clothes I had worn earlier. While I was dressing I continued to drink from the bottle as Old Joe was playing close attention to my consumption. When the bottle was about half-gone Old Joe took the bottle and said that was enough for now.
Old Joe stood up and told me to follow him. I heard the little bag of money jingle as we started back in the direction of the tavern. I asked him how much money they had made off of me, and he said it was more than they had made off of any other cabin boy before. He smiled at me and told me that if everything went well they would make a lot more before the next few days were through. He then informed me that we were going to meet the man who owned the tavern and the building we had just used. He also said that before the night was over the owner would probably want to have some fun with me.
As we got to the side of the tavern we turned and went to the back. Old Joe knocked on the door and the Captain opened it. When we entered Old Joe handed the Captain the bag of coins he had collected from the men I had serviced. The Captain grinned at me as he tested the weight of the little bag in his hand. He could tell from the weight that we had collected a lot more than he was expecting.
I looked around the room and noticed that the Captain and a man who had apparently had more than his share of food and drink during his life had been drinking some wine while waiting on us. The man was well over three hundred pounds and looked as if he had been forced into the chair he was sitting in. He had a big grin on his face and I thought I saw some spit drool down his chin as he looked me over. He reached out his hand at me and Old Joe pushed me in his direction. He grabbed my wrist and pulled me beside him and then turned me around as he squeezed my ass. He then ran his hand between my legs from behind me and reached up and fondled my cock and balls.
Even though many men had used me this sort of sampling of the meat on the hoof was a little embarrassing to me. Old Joe noticed the red on my face and giggled a little at me. The Captain looked at the man and asked if they had a deal. This time I am sure he was drooling as he said yes. The Captain then looked at me and told me that I was to spend the night with the man, but I didn't have anything to worry about. The man would not hurt me and I probably would enjoy it.
The man looked up at the Captain and wanted to know it Old Joe was also going to stay with him. Old Joe told him he would never miss a chance to stay with the man. The Captain smiled and said his good byes as he left me and Old Joe there with the man.
Old Joe started pushing a couple of cots together as the man reached up and started removing my clothes. He had me completely naked and had pulled me into his fat face. He gobbled my cock into his mouth before I even knew what he was doing. My cock knew as it quickly got hard. The man was pushing my cock down his throat and then pulling it all the way out before forcing it back in.
Old Joe told him that the bed was ready as he pulled my cock out of his throat and then pushed me away as he strained to get out of the chair he was in. When he stood up Old Joe reached out and helped him loosen his pants as they fell to the floor. When he pulled his shirt over his head I was face to face with a couple of breast that would have been to large for any woman to carry around. The man grabbed them and pulled the nipples up to his mouth and sucked each one into his mouth.
He held his breast out away from his chest as he told me to suck on them. I leaned in and was a little surprised as I noticed how hard the nipples of the breast were. Just when I was really getting into sucking on them he pulled them away and went to the bed. He lay down on his back and told me to straddle his chest as he pulled his breast up and dropped them on his shoulders. When I straddled him he took his breast and squeezed my cock between them.
His breast completely covered my cock and I was getting really excited from the heat that the two were creating. He told me to start pumping as he held the breast in place. I was getting out of control again but this time I wanted to do the fucking instead of getting fucked. I had almost worked myself up to an orgasm when he told me to stop and get off of him. When I had gotten up he rolled over on his stomach and pulled his knees as far as he could underneath himself. I was standing there looking into a fat hairy ass that had bright pink asshole right in the middle of it.
Old Joe moved in beside me and poured a little oil right on the asshole and then pushed me towards it. I didn't have to be told as I forced my cock all the way inside with one push. The fat man grunted when I first entered but started moaning as I started pumping in and out. I was so excited that I came with a couple of minutes. The man raised up which forced me back and out of his asshole.
He turned on his side with his ass on the edge of the bed. He pulled me down and beside him as he pushed my head toward where his cock should be, but I only noticed some pubic hair. Old Joe noticed the look on my face as he reached down and pushed his fingers into what appeared to be a hole in the mound of fat above the man's balls. As he pulled his finger out I noticed the head of the man's cock as it started growing and coming out of the hole. I quickly sucked the head into my mouth and got a bitter taste of pee and dry cum. I started sucking and licking as his cock got longer and harder. There were about three inches of shaft and the head of the man's cock that I could get in my mouth
Old Joe grabbed the man's leg that was above my head and placed it in a sling that was tied above the bed. This allowed me to move my head around freely while I sucked his cock and fondled his balls. While I was working over his cock I noticed that Old Joe was applying oil to his monster of a cock as he was preparing to fuck the fat man.
I could feel the fat man's muscles as they tightened up when Old Joe pushed his cock half way inside. Old Joe was showing no mercy as the man grunted and then swallowed my cock. He was making squishing noises as he tried to swallow my cock and balls. Old Joe had managed to force all of his cock inside the man's asshole and was now pounding his cock into the man as fast as he could.
After a few thrust I felt the hot cum of the fat man as it splattered on the back of my throat. He shot about six times before he stopped, but neither he nor Old Joe stopped what they were doing. Within another minute I was drinking his cum again and this time I let my own cum fly into his mouth. He never missed a breath as he swallowed and continued to suck my cock. This continued on for about thirty minutes until Old Joe finally couldn't take anymore as he filled the fat man's ass full of cum. He pulled his cock out of the man's asshole and sat down in the chair.
The man removed my cock from his mouth and told me that I could stop sucking on his. I watched as his cock withered away and disappeared inside the mound of fat and hair. Even though it had only been a few minutes since I had cum my cock was still hard. As the man rolled over on his back I as still staring at the hole where his cock should have been. He noticed me looking and reached up and grabbed the bottle of oil and poured some inside the hole. He then had me move to where I was right in front of him and then push my cock into the hole where his cock was.
The fit was a little tight but the oil helped as my cock slipped inside with his cock. The fat man pushed the mound of fat up toward me as I started fucking it like it was a pussy or some man's asshole. I didn't last long before I was filling the little hole full of cum. As I pulled my cock out it was covered with cum and Old Joe leaned down and cleaned it off with his mouth. He pointed to the hole that was oozing cum. I leaned over and started licking my cum up as it ran out of the hole. I started sucking and then pushing my tongue deep in the hole, cleaning up all the cum I could get too.
I felt his cock as it started growing again and was pushing the rest of my cum out of the hole. As his cock came out I sucked and licked ever bit of it clean. The man was really enjoying the attention and just when I thought I was through, I noticed his cock was about to explode. I pushed his cock in my mouth just as the first volley came flying out. I was able to swallow all of his cum.
After a few minutes he rolled over on his side and asked which of us were ready for some more fun. This continued on for most of the night until the fat man finally dozed off for the remainder of the night. Old Joe and I both took that as a clue to try and get some sleep before he woke up again. As I was falling to sleep I was trying to think what the next day was going to be like.